ANTIMETABOLITES PRODUCED BY MICROORGANISMS. VI 1) L-N5-(1-IMINOETHYL) ORNITHINE

JAMES P. SCANNELL; HELEN A. AX; DAVID L. PRUESS; THOMAS WILLIAMS; THOMAS G. DEMNY; ARTHUR STEMPEL

doi:10.7164/antibiotics.25.179

The Journal of Antibiotics

Online ISSN : 1881-1469
Print ISSN : 0021-8820
ISSN-L : 0021-8820

ANTIMETABOLITES PRODUCED BY MICROORGANISMS. VI ¹⁾ L-N⁵-(1-IMINOETHYL) ORNITHINE

JAMES P. SCANNELL, HELEN A. AX, DAVID L. PRUESS, THOMAS WILLIAMS, THOMAS G. DEMNY, ARTHUR STEMPEL

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1972 Volume 25 Issue 3 Pages 179-184

DOI https://doi.org/10.7164/antibiotics.25.179

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Abstract

A new antimetabolite of arginine and metabolically related compounds was isolated from a fermentation broth produced by an unclassified Streptomycete. The structure was shown to be L-N⁵-(1-iminoethyl) ornithine and the compound was synthesized by reaction of the copper complex of L-ornithine with ethyl acetimidate. Mild base hydrolysis of the compound gave the expected products, L-ornithine and L-N⁵-acetylornithine and, in addition, a rearranged product, L-N²-acetylornithine. Arginase hydrolyzed the antimetabolite to L-ornithine.

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